


Virgin

by orphan_account



Category: Villainous (Cartoon)
Genre: M/M, NSFW, Porn Without Plot, submissive black hat
Language: English
Status: Completed
Published: 2017-06-12
Updated: 2017-08-10
Packaged: 2018-11-13 08:56:32
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 4,737
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11181354
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: Nobody's ever been foolish enough to bed an Eldritch Horror before





	1. Chapter 1

**Author's Note:**

> thanks to an anon for this promt

“Alright sir, just spread your legs… yes, just like that, you’re doing so good sir.”

Flug ran his free hand down his bosses thigh, attempting to sooth the tremors passing through the leg muscles. It seemed to help a _little_ , although given that Black Hat’s whole body was shaking, it didn’t seem to matter that much in the long run.

Flug’s other hand was currently busy jacking his boss off.

He didn’t know which was odder; the situation he’d found himself in, or the fact his boss had tentacles for a dick. Several, in fact. Although, as he stroked them, he found only the largest was getting slick with some kind of natural lube, while the other much thinner ones were simply holding on to Flug’s wrist and arm, curling around him in a way that suggest it didn’t want him to ever let go. Perhaps this was a natural reaction to being touched on Black Hat’s part, or maybe it was simply instinct.

Flug would bet on the latter. He returned his gaze to his bosses face, watching as the demon struggled not to come undone right then and there. Black Hat looked _completely_ out of it, face flushed and breath coming in short bursts, his body tensing and relaxing with each stroke of Flug’s hand. He was _completely_ at the scientists mercy.

“Can you lay down for me?” Flug whispered, reaching a hand up to cup Black Hat’s cheek. The other struggled to refocus his gaze for a moment before uttering a wheezing sound that was probably supposed to be his answer, before Black Hat gave up and nodded.

Black Hat clenched the sheets like a lifeline as he lowered his body slowly and carefully, as if afraid he’d break himself if he moved just a little too fast. Once he was fully settled Black Hat rubbed the side of his face into a pillow, his hands and clawed feet digging into the mattress under him.

“You’re doing so good, sir.” Flug promised.

“ _Hrmmmmmm_.” was Black Hat’s elegant reply. “J-Just…-” Black hat began, stuttering for a moment before falling silent. His gaze returned to Flug as he panted, his tentacle curling around itself twice as it sought out more friction. “N-eed ma-more…”

Flug planted a kiss on the corner of Black Hat’s mouth, trusting his boss was too out of it to get worked up over the display of ‘lovey dovey’ emotion. That had been Black Hat’s one complaint when he’d dragged Flug in here to lose his own virginity…. That humans were too _personal_ for his taste.

Flug had a feeling his bosses real problem was the fact no one else had been willing to get personal _enough_ for him. This was all new territory for the demon, and Flug couldn’t help but feel a flutter of pride in his chest that he was the first person to make Black Hat react like this, the _only_ human to have ever wielded such power over the galactic _terror_.

“Ready for something new, sir?” he asked.

Apparently he was, since Black Had immediately yanked Flug’s body flush to his own, hands drifting over every inch of the humans skin as he attempted to kiss him through that bag of his. Flug took this as a ‘yes’, grabbing Black Hat’s wrists for a moment so he had the wiggle room to straddle the others waist, looking back to locate that tentacle he’d pinpointed as the others cock.

He was trying to take this slow, but apparently the tentacle had other ideas. It rubbed itself against Flug’s bottom, finding an opening and diving inside of him in one go. Flug jerked as it filled him, the appendage filling Flug in a way he’d never even considered before. He couldn’t help a sigh of relief at that slight sting of being stretched in just the right way, grinding the hips down on the cock as he worked his body lose on it.

“Eager, are you?” Flug asked, his voice coming out in a gasp. The demon was a mess under him, his voice what Flug could only describe as a _coon_ as the others back arched into Flug’s body, claws tearing into the sheets as Flug adjusted himself above him.

That was okay, Flug wasn’t really expecting a verbal response anytime soon. Instead he readjusted his knees on the bed so he could pull himself off the cock hilt deep in his ass, his boss cring out from the loss. It didn’t last long, his sounds returning to moans once Flug began to sink back down over his shaft.

“Easy now…” Flug muttered. The tentacle easily slid back into his body, twisting about in a way that made it feel even bigger inside of him.

Neither of them could wait.

Flug braced his hands against the others chest, letting himself rise and fall faster and faster until the sound of skin slapping against skin filled the room, Flug gasping as he let himself go to the pleasure. Amazing stress reliever, really.

Black Hat arched under the movement, hands scratching at the sheets as the other smaller tentacles wrapped around Flugs thighs, holding onto him. The demon began thrusting his hips in time to Flug’s rising and falling body, trying to get every inch of himself in and out with each thrust.

Now it was Flugs turn to find himself speechless, working himself faster over the tentacle as he played with himself. Maybe he should have seduced his insult-to-all-things-sane boss _years_ ago-

The tentacles movement suddenly went _crazy_ , Black Hats noises taking on a new, higher pitch. It was all the warning Flug was gonna get was get out of the demon, reaching down to touch himself so he could push himself over the edge as well.

The tentacle pulsed inside of his body before something thick and hot, flooded his insides and dripped down Flug’s inner thigh. Flug kept riding the cock throughout it, stroking himself to a climax and spilling his own semon onto his hand.

Black Hat collapsed on the bed, Flug following suit as he half laid on his bosses chest, letting the tension melt out of his body and just enjoy being on cloud nine for a little while longer.

Once he was back to his senses, Flug realized his boss was asleep. He pushed himself up onto his elbows, watching the gently rise and fall of Black Hat’s chest. He slept as gracefully as an overturned bull, but Flug couldn’t help but admit to himself that he enjoyed the sight.

Well, time to get cleaned up. Then, a nice long nap.


	2. Too much sex

Ever since Flug had helped his boss lose his virginity, he’d been getting jumped for sex at every corner. 

At first, he couldn’t  _ really _ complain. Black Hat was quickly getting  _ good _ in bed. Flug liked to think that was because he was a good example. Plus, Black Hat had been far less tense ever since he’d started sleeping with his employ. That probably wasn’t ethical, but hey, they were villains after all. 

But it was rapidly becoming a problem when his boss didn’t let him get any actual  _ work _ done. Even so, a guy could only take so  _ much _ sex before he needed to  _ rest _ once in awhile. Refractory periods and all that. 

He drew the line at his boss following him into the shower. Nope, no, not at all. He was not down for shower sex, that was when he got  _ cleaned _ , not for just getting himself  _ even dirtier _ . Besides, what if he slipped and broke his neck? Or hurt his dick? God, that would be  _ embarrassing _ . 

“Sir, stop.” Flug said, placing his hand on his bosses chest and pushing him into the bedroom. There was a time when he’d never have  _ dared _ tell his boss what to do, or push him around.  _ Literally _ push him. But hey, once you’ve ridden a guys cock a few times, you got cocky yourself. 

“We’ve had  _ more _ than enough sex recently.” Flug said, crossing his arms. “In fact, you barely let me out of your bed for the first  _ three _ days we started sleeping together. I need time to work and rest before we do anything else. I’m only human, after all.”

Black Hat looked confused, but so long as he wasn’t getting angry, Flug was sure he could- possibly- stay safe enough to stand his ground. Hopefully. 

“I thought you liked sex?” Black Hat asked, clearly missing the point. Flug huffed, rubbing the place on his bag where the bridge of his nose would be.

“Of course, sir, but… you can’t expect me to have sex with you at the drop of a hat.” Flug sighed, exasperated. “Look, why don’t you just… Demecia’s been asking you for this for years, why don’t you go spend some time with her? I’ll still be right here once you get back.” 

“Girls can have sex?” Black Hat asked. Flug stared at him. Did he… not know how humans reproduced? How did… did sex have anything to do with Black Hat’s own reproduction cycle?

… Now was not the time to ask these questions. 

“Er- yes, of course they can.” Flug began, intending to say more. Instead, Black Hat spun on a heel and briskly walked out of the room, letting the door slam shut behind him. 

Flug resisted the urge to flop into his bed, electing, instead, to head back into the bathroom. 

 

\---

 

“How many…. ‘toys’ , do you have?” Black Hat asked. 

“Oh, lots.” Demecia chirped, adjusting her strap on. “I can show you plenty later. Now, make sure you’ve  _ reeeally _ stretched yourself, it can hurt to lose your anal virginity if you aren't prepared for it.”

Black Hat was fairly certain he’d ‘stretched’ himself more than enough, considering he’d gotten two of his fingers to the knuckle inside of himself. Besides, what was he, putty? No. He was a shapeshifter. If there wasn’t enough room for that toy inside of him, he’d  _ make _ room. 

His cock was  _ bigger _ than that thing, and  _ Flug _ could take his cock without any trouble. He refused to let himself  _ lose _ to his own employee, even if they weren't actually competing. 

Above him, Demencia scurried herself closer to his lower body, her hands pushing his legs further apart. At this point, they were closer to his waist then too each other. Thankfully, the form he’d chosen was  _ very _ flexible, as Demencia had surly noticed. 

She’d also noticed his cocks squirming around, having gotten worked up as Black Hat had fingered himself open. Demencia reached down, shoving her hand into the nest of tentacles and- oh  _ Cthulhu _ did that make him see  _ stars _ . In a  _ good _ way. 

“H-Hurry up already~” Black Hat growled, the effect somehow ruined when he proceeded to moan as Demencia’s fingers somehow did a thing where they pumped the shaft while her thumb moved in little swirls over the tip. And he thought  _ Flug _ gave good handjobs-

Regardless, Demencia actually  _ listened _ to him for once, aligning that toy of hers with his lower body. She couldn’t seem to help but tease him immediately after, grinding the shaft of her toy against his asshole instead of giving Black Hat what he  _ needed _ . 

“Demencia-” Black Hat gasped, arching up into what touches he was getting. “ _ Now _ .”

Demencia licked her lips, giving him a bright, bubbly smile, before alining herself with Black Hat’s hole and finally starting to slip inside, wiggling her hips in an attempt to gauge how test how tight he was. For Black Hat, it was  _ too slow _ , the slide of the toys shaft inside him making him realize how desperately he needed  _ more _ of that  _ now _ . 

He made a hissing sound- thought it once again faded into a moan as Demencia somehow settled fully inside of the demon, causing Black Hat to shove his upper half against the bed to better lift his hips, scratching at the sheets as he was flooded with a foreign feeling.

How did Flug  _ stand _ after feeling something like this?

And then Demencia  _ moved _ . What Black Hat thought was good was  _ shattered _ under the steady thudding of the toy against his insides, reminding Black Hat of that spot he’d noticed when stretching himself. The skin had felt softer than normal, and had made his tentacles active when he’d brushed his fingers over it. And yes, it had felt  _ good _ . 

He shifted his hips, experimenting with the different angles he could get Demencia to thrust into him, trying to figure out which angle would give him the most pleasure the fastest.

Boy, did he find it. 

The moment Demencia began thrusting into that  _ one spot _ , Black Hat’s mind hit the floor as his highest level thought was something along the lines of  _ moremoremore _ or  _ yes, right there _ . His back arched up into a perfect black rainbow, his own top hat obscuring his view at this point. 

Demencia said something above him that was lost on the demon, his only response a pleased sounding noise. His hands tore away from the bed to shove themselves into his own cocks, pleasuring himself as his toes curled to be nearly entirely closed. His body  _ rolled _ with each thrust, allowing the pleasure to begin coiling in his stomach in a familiar sensation. 

Suddenly, Black Hat’s hat was shoved out of his face so Demencia had room to  _ kiss _ him, their lips locking despite the way Black Hat’s body jerked with every thrust. Her own talented hand took over stroking Black Hat’s cock, and his moved to her back. He attempted to yank her closer, sharp claws likely leaving thin red lines across the skin. Surprisingly, that seemed to only make her thrust  _ faster _ . 

Black Hat wrapped his legs around the girl, his whole body jerking as waves and waves of pleasure spilled into him, his green cum spilling between their pressed bodies and over Demencia’s hand. The girl waited until the shivering stopped to pull out, slowly dragging that toy out of Black Hat’s clenched ass to be tossed aside onto her messy floor. She’s clean it up later. Probably. 

“Just wait until you try the ones that vibrate~” Demecia giggled. 

Black Hat wasn’t sure what that meant, but from the way she was acting it seemed to be more  _ good _ stuff. He would definitely be returning to her for more sex… but then again, he liked Flug too. Maybe he could get both of them into the bed at the same time. 

Yeah, that sounded like a good idea. For now, he needed to pass out. How either of his employees managed to keep going after something like  _ that _ , he’d never know. 


	3. Threesome

**Summary for the Chapter:**

> Black Hat's been pestering his lovers for a bit too much sex lately- it's time he get his punishment.

Black Hat tugged his bonds, struggling for a moment with the conflicting needs to break free and the ones that reminded him he’d be giving up sex for a  _ month _ if he did. 

It wasn’t even the most complex trap he’d been in. While he’d slept last night someone had handcuffed his wrists together, looping the chain around a thin pole attached to his headboard. Two more cuffs kept his legs stretched out towards the bottom of his bed, where they were each cuffed to one of the poles at the corners of his bed. 

Above his face, Demencia’s hips bobbed lower for a moment, just long enough for him crane his neck up and slip his long, serpent like tongue between those heavenly folds. Demencia gave a surprised yelp from the pleasure, yanking her hips off his tongue and once more out of his reach. 

“H-hey, this is supposed to be a  _ punishment _ , remember?” Demencia called back to him. Black Hat whined in response, licking his lips as he yearned to join his lovers in their embrace. 

Flug and Demencia had their lips locked together, hands freely exploring each others bodies. One of Demencia’s skilled hands was on Flug’s cock, pleasuring the man while Flug played with her boobs, seemingly enjoying the feel of them in his hands.

Demencia was hovering so,  _ so _ close to his face- her pussy just out of reach most of the time, no matter how much he stuck out his tongue or stretched his neck. Without shape shifting, of course. 

As for Flug, he was too far up his chest for his tentacles to reach, nor could he curl his lower body to get closer. It didn’t help that the sight above him was nearly enough for him to orgasim on his own, he just needed a  _ little _ more. 

It wasn’t that he couldn’t shapeshift out of his bonds, or break free with a flick of his wrists. Nothing built on or in  _ this _ planet was enough to cage him- but his lovers swore they wouldn’t touch him for a  _ month _ if he dared. 

“You know, I think he’s ready for the next part of his punishment~” Demencia chirped, reaching down to pap Black Hat’s side. Black Hat perked up, wondering what the two had planned that was worse than  _ this _ . Pain would never do, he’d probably  _ like _ that. 

Flug jolted, surprised by Demencia’s suggestion, before pulling his hands away from the others busty form. 

“A-ah… oh, sure.” he said, shrugging. He reached back to where he’d dumped his pants near to bottom of the bed, slipping his hand into the back pocket and pulling out a thick, silver ring that looked like it would fit around the base of his cock. 

Wait a minute. 

Flug fiddling with it in his hands, the ring popping open on one side from some unseen button press. Flug confirmed Black Hat’s suspicion when he reached behind himself to grab the demons cock, holding it out straight while he slipped the ring around his base, snapping it shut. After a moment it tightened, leaving a strange feeling in Black Hat’s groin. 

Without another word, the two changed positions, Demencia sitting down on Black Hat’s crotch, leading Black Hat’s cock to slip into her ass. Black Hat himself couldn’t help but moan, trying to press up into her. It felt so,  _ so _ good to fill something, he almost forgot he was being punished-

And then Flug moved on top of her, their legs spread to give their boss a perfect view as Flug’s cock pushed itself into Demencia’s pussy, causing the girl to cry out in pleasure. Black Hat was half sure she was being loud just to  _ tease _ him, and half because Demencia was  _ always _ loud. 

Flug adjusted himself, one of his hands noticeably returning to Demencia’s boobs as he began to move his hips, starting with slow, short movements as they both adjusted to the position. 

He might as well have been pounding her for how much it was affecting Black Hat. His eyes were locked on the spot where their bodies met, panting as if he’d just run a marathon. Black Hat wiggled his hips in an attempt to get some friction on his own cock, but the weight of the two kept him pinned. Suddenly the pressure he could feel felt a lot less like a blessing. 

Flug and Demencia moaned loudly in each other's arms, each of their bodies rolling with each thrust in a way Black Hat had never quite  _ appreciated _ before this moment. He was painfully aware of the cock ring imprisoning any hope of orgasming from the sight of his lovers making out on his dick, no matter how tightly Demencia’s body pressed down around it. 

Demencia held her legs open, giving Flug more room to really start  _ pounding _ into her, the man's orgasm clearly building faster than her own. Still, Black Hat noticed that Flug was fiddling with this weird bit of skin near the top of Demencia’s pussy, which seemed to be making Demencia cry out louder. 

Flug didn’t last another full minute before giving a hard  _ slam _ inside Demencia and freezing, shuddering before pulling out a few moments later, a few bits of his own semon dripping out onto his bosses chest. 

Black Hat had assumed the show was done then, but he was dead wrong. It was only half over. 

Flug shifted to the side, still giving Black Hat a clear view of Demencia’s spread pussy before he started rubbing that bit of skin at the tip again, moving his mouth close to it and licking it slowly, drawing a long sound out of Demencia as if she’d lost the ability to say any actual words. 

Flug moved his mouth over the skin, his cheeks pulling in slightly as he sucked on it, tongue presumingly still rubbing against it. 

Black Hat wanted that mouth around his own cock more than anything else in the world. 

Demencia’s voice rose higher and higher, into a pitch Black Hat had never heard before, before her whole body shuddered as she came above him, her own cum spilling out onto his chest to mix with what semen of Flug’s was still there as well. 

Black Hat whined as Demencia pulled off his cock with a slow  _ pop _ , the friction reminding him he was as hard as ever. Still, neither of them seemed to be in any rush to touch him. 

“You’re so messy Flug, and here I thought  _ you _ were the one who had to clean up when you and Black Hat fucked.” Demencia complained, hovering over Black Hat’s chest as her pussy leaked a few more thick drops onto him. “You might as well have-”

She paused suddenly, a smile nearly splitting her face as a thought occurred to her. 

“Oh Blaaaaaacky~” she purred, crawling up and placing both of her hands on either side of Black Hat’s head, hovering above him. “I think you’ve earned a chance to redeem yourself, hmm?” she teased. 

Black Hat nodded, mouth opened to draw in as much cooling air as he could get, which was apparently exactly what she wanted. Demencia straightened herself up, pulling herself up to the headboard and lowered her ass over Black Hat’s face, who wasted no time pushing himself into her and lapping as her pussy, shoving his tongue inside. 

Demencia screamed out in pleasure as her still sensitive insides were assaulted by Black Hat’s tongue, his tongue curling in several ways that made her shudder until he someone found the  _ exact _ way that made her arch her back and moan the loudest. 

Apparently, his tongue was much longer than she’d thought it was, as she gave several cries of surprise as he pressed his tongue  _ deep _ inside of her, pulling out a few times to lap at her folds before shoving his tongue back in.  

While he ate her out, Black rubbed the space between his eyes and mouth against that bit of skin that he’d seen Flug press against before. Apparently she  _ really _ liked that, as she came moments later with a loud moan. Black Hat lapped up every inch of her he could before she pulled away, shuddering with a big goofy grin on her face. 

“A-ah, I think he’s e-earned his freedom, huh F-Flugsy?” she asked, nearly collapsing on the bed. 

“How can he tell, he hasn’t done it yet.” Black Hat pointed out. For a moment the other two were silent, before Demencia suddenly sprang up and leaped on Flug. 

“Oh, he’s right!” she chirped, suddenly full of energy.

“D-Demencia, I just came!” Flug stuttered, trying to pull himself free. “Give me a break before I do anything else!”

Black Hat licked his lips. 

“Flug, if Demencia can cum right away like that, so can you. Get over here.” he ordered. 

Demencia shoved Flug forward despite his protesting, forcing him to get up close and personal with Black Hat’s mouth. 

“W-wait- stop, now l-lets just talk about this for a momeHAH, AHHHH~” 

Black Hat felt a spark of pride when Flug lost his voice mid sentence. He might not be allowed to shapeshift right now, but if he  _ already _ hadn’t bothered to shapeshift himself a gag reflex… well, Flug didn’t seem to be complaining while his cock was buried somewhere in the back of his bosses throat. 

Black Hat curled his long tongue around and around the shaft, letting it rest in his throat for now as he sucked it off, watching as Flug shuddered and struggled to stay upright above him. Ah, the glory of not needing to pull off for air. 

He could  _ feel _ the piece of flesh in his mouths struggle to pump itself with fresh blood- but get hard it did. Flug rocked his hips, effectively fucking Black Hat’s throat.  _ Hah _ , needed a  _ break _ , sure. 

Flug spilled his load  _ much _ faster than he had with Demencia- with less cum than he normally gave as well. A shame, but then again, Flug  _ was _ only human. Though, Demencia didn’t seem to have this problem. Maybe girls were better at sex?

Flug pulled off, sighing in relief before giving a surprised yip when Black Hat licked the tip of his softened cock, before chucking at the scientist. 

“Have I earned my freedom, doctor~?” he asked Flug, his voice smooth as silk. Flug didn't seem to be in any condition to answer, but Demencia sprang forward, pulling a key out of her hair.

She unlocked something above his head, the cuffs springing lose from his wrists. Black Hat shifted out of the cuffs at his ankles, spinning the three of them around so his lovers were on their back, Black Hat know hovering above them.

Flug gulped, while Demencia giggled cheerfully.

“Such a tease… both of you.” Black Hat purred, tentacles emerging from his back to wrap around the other two, sliding around their arms and legs. “You should have known you’d just get me more worked up. Now, I think it’s only fair you two repay the favor.”

Black Hat ran a hand down his chist, slipping it around his cock and stroking himself, a shudder passing through his body as a moan escaped his lips.  _ Ah _ ,  _ finally _ . 

But as much as he’d love to see how his seed looked dripping from his lovers, he couldn’t cum  _ just _ yet. He tore his hand away from himself, taking a deep breath to calm himself. With a snap of his fingers, the tentacles brought his lovers closer, Black Hat placing his hands on their heads to pull them closer to his groin. 

Demencia beamed at him before opening her mouth wide, her tongue dragging up the shaft  _ agonizingly slowly _ for someone normally so energetic, her tongue flattening itself against the shaft and wrapping around it. Flug’s face was bright red- he was so cute when he got flustered, it was a shame he normally covered it up with that paper bag of his. 

“Hurry up Flug, you don’t want Demencia to get all of my treat, do you~” Black Hat teased, nudging Flug towards his cock. Flug’s eyes flicked from the cock to Black Hat and back again, before edging closer and sticking his tongue out to lick at the shaft, pressing his mouth to it to kiss and suckle up the skin. 

Black Hat moaned, shutting his eyes and letting his head fall back as his lovers worked, his cock curling against their faces as they worshiped it, dripping from his glow in the dark seed from the tip. As if the bed wasn’t stained enough at this point. 

_ Oh _ , their mouths were more than  _ worth _ the wait- Black Hat jerk his hips as he struggled not to come undone right then and there, wanting to savor this moments. Someone held the side of his cock, keeping it still as those  _ wonderful _ tongues worked away, liquid pleasure flowing over his shaft. A whimper emerged from Black Hat as his will cracked, that little swirling pot of pleasure in his cut threatening to spill over. 

Oh,  _ fuck _ . 

With a loud snarl, Black Hat finally spilled over the edge, his cum spurting out onto his lovers faces. Flug yanked back in surprise, Demencia giggling and just licking his cock through the orgasm, making Black Hat twitch and cry out as his sensitive nerves were played with. 

The tentacles disappeared into black mist, Black Hat falling between his lovers with a content sigh. That after-sex haze was back, and he purred as he felt the warmth of his lovers at either side of him.  He made a pleased sound, his mind failing him when it came to words right now. 

When he woke up again, they were  _ definitely _ doing that again. 


End file.
